Missing or compromised permanent molars can complicate orthodontic treatment planning and mechanics. Molar extraction should be considered in appropriate situations, but clinicians must decide between closing and regaining the edentulous space. Several factors should be taken into consideration to achieve appropriate molar space management, such as the need for space, asymmetry, periodontal status, sinus pneumatization, and the terminal molar position. Herein, three sample cases are reported to demonstrate the treatment options for molar space closure and maintenance with these factors taken into consideration during treatment planning. The understanding of mechanics played a crucial role in anchorage preparation and side effect prevention. If the third molar substitution was managed in advance and adequate space between the ramus and third molar was obtained via second molar protraction, the tooth spontaneously erupted in a favorable position without requiring further treatment. This case series can aid clinicians in molar space management. Regardless of whether the space is to be closed or regained, the treatment plan should conform to the patient’s expectations and improve occlusion with minimal side effects and treatment duration.